Acetonitrile → 3-(2-Bromophenyl)propanenitrile

Temperature

-78 °C

Into a 500-mL 3-necked round-bottom flask, was placed a solution of acetonitrile (49 g, 1.20 mol, 9.96 equiv) in tetrahydrofuran (150 mL). This was followed by the addition of BuLi (72 mL, 1.50 equiv) dropwise with stirring at −78° C. Stirred at −78° C. for 1 h. To this was added a solution of 1-bromo-2-(bromomethyl)benzene (30 g, 120.00 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) dropwise with stirring at −78° C. The resulting solution was stirred for 1 h at −78° C. The reaction was quenched by the addition of 100 mL of water at −78° C. The resulting aqueous solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). The crude product was purified by distillation under reduced pressure (2 mm Hg) and the fraction was collected at 98-107° C. This resulted in 13.21 g (52%) of 3-(2-bromophenyl)propanenitrile as colorless oil.

1. customInto a 500-mL 3-necked round-bottom flask, was placed
2. stirringStirred at −78° C. for 1 h
3. stirringwith stirring at −78° C
4. stirringThe resulting solution was stirred for 1 h at −78° C
5. customThe reaction was quenched by the addition of 100 mL of water at −78° C
6. extractionThe resulting aqueous solution was extracted with 3×100 mL of ethyl acetate
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuum
9. distillationThe crude product was purified by distillation under reduced pressure (2 mm Hg)
10. customthe fraction was collected at 98-107° C
11. customThis resulted in 13.21 g (52%) of 3-(2-bromophenyl)propanenitrile as colorless oil

ORD record

ord-0e290a441da643e29e427d26af0133ec

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916560B2